5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 618119-01-0
• Molecular Formula: C₅₉H₆₆O₁₂
• Molecular Weight: 967.166
• Mol file: 618119-01-0.mol

Synonyms:5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

There total 6 articles about 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 60.0%

pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (131684-73-6) → 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (618119-01-0)

Guidance literature:

pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside; With 9-borabicyclo[3.3.1]nonane dimer; In tetrahydrofuran; toluene; at 50 ℃; for 18h;

With sodium hydroxide; dihydrogen peroxide; for 4h;

DOI:10.1016/S0008-6215(03)00255-6

Reference yield:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) → 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (618119-01-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / 4 Angstroem molecular sieves; MeOTf / diethyl ether / 17.5 h / 20 °C

2.1: 9-BBN / toluene; tetrahydrofuran / 18 h / 50 °C

2.2: 60 percent / aq. H₂O₂; aq. NaOH / 4 h

With 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/S0008-6215(03)00255-6

Reference yield:

D-Glucose (2280-44-6) → 5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (618119-01-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 63 percent / CSA / 48 h / 140 °C

2.1: 46 percent / CSA / dimethylformamide / 7 h / 65 °C / 195.02 - 210.02 Torr

3.1: NaOH; Bu₄NHSO₄ / CH₂Cl₂; H₂O / 46 h / 41 °C

4.1: 80 percent / 4 Angstroem molecular sieves; MeOTf / diethyl ether / 17.5 h / 20 °C

5.1: 9-BBN / toluene; tetrahydrofuran / 18 h / 50 °C

5.2: 60 percent / aq. H₂O₂; aq. NaOH / 4 h

With sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; 4 A molecular sieve; camphor-10-sulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; methyl trifluoromethanesulfonate; In tetrahydrofuran; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0008-6215(03)00255-6

upstream raw materials:

pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

D-Glucose

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

n-Pent-4-enyl alcohol